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Acetone → HCID 59632050、化合物

HRID 2369053
ノート
印刷プレビュー

反応式

HRID 2369053 の反応式
[Li+].[BH4-].C[O:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=3)=[CH:15][CH:16]=2)[N:9]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[N:8]=1)=O.CC(C)=O.O>C1COCC1>[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:9]1[C:10]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:24])=[O:25])[CH:18]=3)=[CH:15][CH:16]=2)=[CH:11][C:7]([CH2:5][OH:4])=[N:8]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 180AcetoneHCID 962WaterHCID 4148881Lithium borohydrideHCID 59631939HCID 59631939、化合物

生成物 1

HCID 59632050HCID 59632050、化合物収率 75.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

LiBH4 (1.0M in THF, 14 mL, 28 mmol) was added dropwise at rt to a stirred solution of 1-(2-chloro-phenyl)-5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1H-pyrazole-3-carboxylic acid methyl ester (4.38 g, 9.26 mmol) in anhydrous THF (100 mL) under N2, and the resulting mixture was stirred at rt for 3d. Acetone (2 mL) and water (2 mL) was added successively at 0° C. and the solid was filtered off. The filtrate was concentrated in vacuo. The residue was taken up in EtOAc (200 mL), washed with water and brine, dried over Na2SO4 and evaporated in vacuo. The crude product was purified by flash chromatography (0-90% EtOAc/hexanes) to give the title compound as a white solid (3.1 g, 75%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.84-7.81 (m, 1H), 7.74-7.72 (m, 1H), 7.58-7.44 (m, 5H), 7.21 (d, 1H), 6.76 (d, 1H), 6.69 (s, 1H), 4.80 (s, 2H), 3.07 (s, 3H), 1.65 (brs, 1H). MS(ES): 445 [M+H]+.

後処理

  1. filtrationthe solid was filtered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography (0-90% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-b50733aef2244f3dbe14fe17f50d742f
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08703805B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート